Substituted herbicidal phenyluracils

ABSTRACT

The invention relates to novel substituted phenyluracils of the general formula (I)                    
     in which 
     m, n, Q, R 1 , R 2 , R 3 , R 4 , R 5 , X and Y are each as defined in the description, 
     to processes for their preparation, to novel intermediates and to their use as herbicides.

The invention relates to novel substituted phenyluracils, to processesand novel intermediates for their preparation and to their use asherbicides.

Certain substituted aryluracils are already known from the (patent)literature (cf. EP-A-255 047, EP-A-260 621, EP-A-408 382, EP-A-438 209,EP-A-473 551, EP-A-517 181, EP-A-563 384, WO-A-91/00278, WO-A-91/07393,WO-A-93/14073, U.S. Pat. No. 4,979,982, U.S. Pat No. 5,084,084, U.S.Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, U.S. Pat. No. 5,169,430,U.S. Pat. No. 5,486,610, U.S. Pat. No. 5,356,863). However, thesecompounds have hitherto not attained any particular importance.

This invention, accordingly, provides novel substituted phenyluracils ofthe general formula (I)

in which

m represents 0, 1, 2 or 3,

n represents 0, 1, 2, 3 or 4,

Q represents O (oxygen), S (sulphur), SO, SO₂, NH or N(alkyl),

R¹ represents hydrogen, amino or optionally substituted alkyl,

R² represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each caseoptionally substituted alkyl or alkoxycarbonyl,

R³ represents hydrogen, halogen or optionally substituted alkyl,

R⁴ represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,

R⁵ represents cyano, carbamoyl, thiocarbamoyl, halogen or in each caseoptionally substituted alkyl or alkoxy,

X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, orrepresents in each case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy,dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino,alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl,alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl,alkinylcarbonyloxy or arylcarbonyloxy, and

Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, orrepresents in each case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy,dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino,alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl,alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl,alkinylcarbonyloxy or arylcarbonyloxy,

where, in the case that m and/or n are greater than 1, X and Y in theindividual compounds possible in each case have identical or differentmeanings from those given, which is to say that X and Y may be identicalor different,

and salts of compounds of the formula (I).

Preferred substituents or ranges of the radicals present in the formulaegiven above and below are defined below.

m preferably represents 0, 1 or 2.

n preferably represents 0, 1, 2 or 3.

Q preferably represents O (oxygen), S (sulphur), SO, SO₂, NH orN(C₁-C₄-alkyl).

R¹ preferably represents hydrogen, amino or represents optionallycyano-, halogen- or C₁-C₃-alkoxy-substituted alkyl having 1 to 4 carbonatoms.

R² preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl orrepresents in each case optionally cyano-, halogen- orC₁-C₃-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1to 4 carbon atoms.

R³ preferably represents hydrogen, halogen or represents optionallycyano-, halogen- or C₁-C₃-alkoxy-substituted alkyl having 1 to 4 carbonatoms.

R⁴ preferably represents hydrogen, cyano, fluorine or chlorine.

R⁵ preferably represents cyano, carbamoyl, thiocarbamoyl, halogen orrepresents in each case optionally halogen-substituted alkyl or alkoxyhaving in each case 1 to 4 carbon atoms.

X preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano,carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl,halogenosulphonyl, represents in each case optionally cyano-, carboxyl-,carbamoyl-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-,C₁-C4-alkoxy-carbonyl-, C₂-C₄-alkenyloxy-carbonyl-,C₂-C₄-alkinyloxy-carbonyl-, C₁-C₄-alkylaminocarbonyl-,di-(C₁-C₄-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-,phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in eachcase 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy,dialkyl-aminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino,alkyl-sulfonylamino, bis-alkylsulfonyl-amino orN-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbonatoms in the alkyl groups, represents in each case optionally cyano-,carboxyl-, carbamoyl-, halogen-, C₁-C₄-alkoxycarbonyl-,C₁-C₄-alkylamino-carbonyl- ordi-(C₁-C₄-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy,alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy,alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.

Y preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano,carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl,halogenosulphonyl, represents in each case optionally cyano-, carboxyl-,carbamoyl-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-,C₁-C₄-alkoxy-carbonyl-, C₂-C₄-alkenyloxy-carbonyl-,C₂-C₄-alkinyloxy-carbonyl-, aminocarbonyl-, C₁-C₄-alkylaminocarbonyl-,di-(C₁-C₄-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-,phenylaminocarbonyl- or benzylaminocarbonyl- substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in eachcase 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy,dialkyl-aminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino,alkyl-sulfonylamino, bis-alkylsulfonyl-amino orN-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbonatoms in the alkyl groups, represents in each case optionally cyano-,carboxyl-, carbamoyl-, halogen-, C₁-C₄-alkoxycarbonyl-,C₁-C₄-alkylamino-carbonyl- ordi-(C₁-C₄-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy,alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy,alkinyloxycarbonyl or alkinyl-carbonyloxy having in each case 2 to 6carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.

The invention also preferably provides the sodium, potassium, magnesium,calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C4-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium anddi-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I),in which m, n, Q, R¹, R², R³, R⁴, R⁵, X and Y have the preferredmeanings given above—insofar as the compounds of the formula (I) containhydrogen atoms attached to O or S.

m particularly preferably represents 0 or 1.

n particularly preferably represents 0, 1 or 2.

Q particularly preferably represents O (oxygen) or S (sulphur).

R¹ particularly preferably represents hydrogen, amino or represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl.

R² particularly preferably represents carboxyl, cyano, carbamoyl,thiocarbamoyl or represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,methoxycarbonyl, ethoxy-carbonyl, n- or i-propoxycarbonyl.

R³ particularly preferably represents hydrogen, fluorine, chlorine,bromine, or represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.

R⁴ particularly preferably represents hydrogen, fluorine or chlorine.

R⁵ particularly preferably represents cyano, carbamoyl, thiocarbamoyl,fluorine, chlorine, bromine, or represents in each case optionallyfluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,methoxy, ethoxy, n- or i-propoxy.

X particularly preferably represents hydroxyl, mercapto, amino, nitro,formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,bromine, sulphonyl, chlorosulphonyl, represents in each case optionallycyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propyl-thio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s-or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-,propinyloxycarbonyl-, butinyloxycarbonyl-, methylaminocarbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino,acetyl, propionyl, n- or i-butyroyl, methoxy- carbonyl, ethoxycarbonyl,n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- ort-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyl-oxy, n-or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy,dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino,propionylamino, n- or i-butyroylamino, methoxycarbonylamino,ethoxy-carbonylamino, n- or i-propoxycarbonylamino,methylsulphonylamino, ethyl-sulphonylamino, n- ori-propylsulphonylamino, or represents in each case optionally cyano-,carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylamino-carbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl,propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl,butenyloxy-carbonyl, ethenecarbonyloxy, propenecarbonyloxy,butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy,propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy,propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy.

Y particularly preferably represents hydroxyl, mercapto, amino, nitro,formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,bromine, sulphonyl, chlorosulphonyl, represents in each case optionallycyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propyl-thio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s-or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-,propinyloxycarbonyl-, butinyloxycarbonyl-, aminocarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino,acetyl, propionyl, n- or i-butyroyl, methylcarbonyloxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl,ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy,methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy,dimethylaminocarbonyloxy, diethylamino-carbonyloxy, acetylamino,propionylamino, n- or i-butyroylamino, methoxy-carbonylamino,ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino,ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in eachcase optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-,bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxy-carbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- ori-propylamino-carbonyl-, dimethylaminocarbonyl- ordiethylaminocarbonyl-substituted ethenyl, propenyl, butenyl,propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl,ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl,propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl,butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy orbutinecarbonyloxy, or represents benzoyloxy.

m very particularly preferably represents 0.

n very particularly preferably represents 0 or 1.

Q very particularly preferably represents O (oxygen).

R¹ very particularly preferably represents hydrogen, amino or methyl.

R² very particularly preferably represents carboxyl, cyano, carbamoyl,thio-carbamoyl or represents in each case optionally fluorine- and/orchlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl.

R³ very particularly preferably represents hydrogen, fluorine, chlorine,bromine, or represents optionally fluorine- and/or chlorine-substitutedmethyl.

R⁴ very particularly preferably represents fluorine.

R⁵ very particularly preferably represents cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally fluorine-and/or chlorine-substituted methyl or methoxy.

X very particularly preferably represents hydroxyl, mercapto, amino,nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each caseoptionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-,chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- ori-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, propenyloxycarbonyl-, methyl-aminocarbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,di-methylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl,n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio,n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethyl-sulphonyl, methylamino, ethylamino, n- or i-propylamino,represents dimethylamino, diethylamino, acetyl, propionyl, n- ori-butyroyl, methoxy-carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, n- oder i-propylaminocarbonyl,dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n-or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylamino-carbonyloxy, dimethylaminocarbonyloxy,diethylaminocarbonyloxy, acetyl-amino, propionylamino, n- ori-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- ori-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- ori-propylsulphonylamino, or represents in each case optionally cyano-,carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylamino-carbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethyl-aminocarbonyl- or diethylarninocarbonyl-substituted ethenyl,propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl,butenyloxy-carbonyl, ethinyl, propinyl, butinyl, propinyloxy,butinyloxy, propenyloxy-carbonyl or butinyloxycarbonyl, or representsbenzoyloxy.

Y very particularly preferably represents hydroxyl, mercapto, amino,nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, sulpho, chlorosulphonyl, represents in each caseoptionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-,chlorine-, bromine-, methoxy-, ethoxy-,.n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propyl-thio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl-, ethylsulfonyl-, acetyl-, propionyl-, n- ori-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, propenyloxycarbonyl-, aminocarbonyl-,methylamino-carbonyl-, ethylaminocarbonyl-, n- ori-propylaminocarbonyl-, dimethyl-aminocarbonyl-, phenylaminocarbonyl- orbenzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methyl-sulphonyl, ethylsulphonyl,methylamino, ethylamino, n- oder i-propylamino, representsdimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylamino-carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl,dimethylamino- carbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy,n- or i-butyroyl-oxy, methylcarbonyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,dimethylaminocarbonyloxy, diethylamino-carbonyloxy, acetylamino,propionylamino, n- or i-butyroylamino, methoxy-carbonylamino,ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino,ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in eachcase optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-,bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxy-carbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- ori-propylamino-carbonyl-, dimethylaminocarbonyl- ordiethylaminocarbonyl-substituted ethenyl, propenyl, butenyl,propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl,ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonylor butinyloxycarbonyl, or represents benzoyloxy.

R² most preferably represents trifluoromethyl.

R³ most preferably represents hydrogen.

R⁵ most preferably represents cyano.

Y most preferably represents hydroxyl, methoxy, represents in each casemeth-oxycarbonyl-, ethoxycarbonyl-, methylaminocarbonyl-,dimethylaminocarb-onyl or phenylaminocarbonyl-substituted methoxy orethoxy, represents methylaminocarbonyloxy, methylcarbonyloxy,propinyloxy, butinyloxy or ethoxycarbonyloxy.

A very particularly preferred group is the compounds of the generalformula (IA)

in which

n, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above asbeing very particularly preferred or most preferred.

A further very particularly preferred group is the compounds of thegeneral formula (IB)

in which

n, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above asbeing very particularly preferred or as being most preferred.

The abovementioned or preferred radical definitions apply both to theend products of the formula (I) and correspondingly to the startingmaterials or intermediates required in each case for the preparation.These radical definitions can be combined with one another at will, i.e.including combinations between the given preferred ranges.

Preference according to the invention is given to those compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (“preferably”).

Particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

Very particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningsgiven above as being very particularly preferred.

Most preference according to the invention is given to those compoundsof the formula (I) which contain a combination of the meanings givenabove as being most preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,are—including in combination with heteroatoms, such as in alkoxy—in eachcase straight-chain or branched as far as this is possible.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitution the substituents can be identical ordifferent.

If the compounds of the general formula (I) according to the inventioncontain substituents with asymmetric carbon atoms, the invention relatesin each case to the R enantiomers and the S enantiomers and to anymixures of these enantiomers, in particular the racemates. In the caseof compounds of the formula (I) having alkenyl substituents, theinvention relates in each case to the possible E and Z isomers and theirmixtures.

Examples of the compounds of the general formula (I) according to theinvention are listed in the groups below.

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given below intabular form.

Q R¹ R² R³ R⁴ R⁵ Y O H CF₃ H F CN — O CH₃ CF₃ H F CN — S H CF₃ H F CN —S CH₃ CF₃ H F CN — O H CF₃ Cl F CN — O CH₃ CF₃ Cl F CN — O H CF₃ CH₃ FCN — O CH₃ CF₃ CH₃ F CN — O H CF₃ H F CN OH O CH₃ CF₃ H F CN OH O H CF₃H F CN OCH₃ O CH₃ CF₃ H F CN OCH₃ O H CN H F CN OCH₃ O CH₃ CN H F CNOCH₃ O H CF₃ H F Cl OCH₃ O CH₃ CF₃ H F Cl OCH₃ O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN Cl O CH₃ CF₃ H F CN Cl S H CF₃ H F CN Cl S CH₃ CF₃ H F CNCl O H CF₃ H F CN SH O CH₃ CF₃ H F CN SH O H CF₃ H F CN NH₂ O CH₃ CF₃ HF CN NH₂ O H CF₃ H Cl Cl OH O CH₃ CF₃ H Cl Cl OH O H CF₃ H H CN OH O CH₃CF₃ H H CN OH O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN SCH₃ O CH₃ CF₃ H F CN SCH₃ O H CF₃ H F CN SO₃H O CH₃ CF₃H F CN SO₃H O H CF₃ H F CN SO₃Na O CH₃ CF₃ H F CN SO₃Na O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN COOH O CH₃ CF₃ H F CN COOH O H CF₃ H F CN COOCH₃ O CH₃CF₃ H F CN COOCH₃ O H CF₃ H F CN COOC₂H₅ O CH₃ CF₃ H F CN COOC₂H₅ O HCF₃ H F CN CH₃ O CH₃ CF₃ H F CN CH₃ O H CF₃ H F CN CH₂Cl O CH₃ CF₃ H FCN CH₂Cl O H CF₃ H F CN CH₂Br O CH₃ CF₃ H F CN CH₂Br O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN COOC₃H₇-i O CH₃ CF₃ H F CN COOC₃H₇-i O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F CN

O CH₃ CF₃ H F CN

O H CF₃ H F Cl

O CH₃ CF₃ H F Cl

O H CF₃ H F Br

O CH₃ CF₃ H F Br

O CH₃ CF₃ H F

O CH₃ CF₃ H F

O CH₃ CF₃ H F

O CH₃ CF₃ H F

O CH₃ CN H F CN

O CH₃ CN H F CN

O CH₃ CF₃ H Cl Cl

O CH₃ CF₃ H Cl Cl

O NH₂ CF₃ H F CN

O NH₂ CF₃ H F CN

O CH₃ CHF₂ H F CN OH O CH₃ CHF₂ H F CN

O CH₃ CF₂Cl H F CN OH O CH₃ CF₂Cl H F CN

O CH₃ C₂F₅ H F CN OH O CH₃ C₂F₅ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN CHO O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ H F CN

O CH₃ CF₃ Cl F CN

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above ingroup 1 in tabular form.

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above ingroup 1 in tabular form.

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above ingroup 1 in tabular form.

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above ingroup 1 in tabular form.

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above ingroup 1 in tabular form.

Here, Q, R¹, R², R³, R⁴, R⁵ and Y each have the meanings given above ingroup 1 in tabular form.

Here, Q, R¹, R², R³, R⁴ and R⁵ have the meanings given above in Group 1in tabular form; X has the meanings given above in Group 1 for Y.

The novel substituted phenyluracils of the general formula (I) haveinteresting biological properties. In particular, they have strongherbicidal activity.

The novel substituted phenyluracils of the general formula (I) areobtained when

(a) halogenophenyluracils of the general formula (II)

 in which

R¹, R², R³, R⁴ and R⁵ are each as defined above and

X¹ represents halogen,

are reacted with naphthalene derivatives of the general formula (III)

in which

m, n, Q, X und Y are each as defined above,

or with alkali metal salts of compounds of the formula (III)

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

(b) aminoalkenoic acid esters of the general formula (IV)

 in which

R² and R³ are each as defined above and

R represents alkyl, aryl or arylalkyl,

are reacted with aryl isocyanates of the general formula (V)

 in which

m, n, Q, R⁴, R⁵, X and Y are as defined above,

or with arylurethanes (arylcarbamates) of the general formula (VI)

 in which

m, n, Q, R⁴, R⁵, X and Y are as defined above and

R represents alkyl, aryl or arylalkyl,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

(c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)

 in which

m, n, Q, R³, R⁴, R⁵, X and Y are as defined above and

R represents alkyl,

are reacted with a metal hydride in the presence of water and, ifappropriate, in the presence of an organic solvent,

or when

(d) substituted phenyluracils of the general formula (Ia)

 in which

m, n, Q, R², R³, R⁴, R⁵, X and Y are as defined above,

are reacted with 1-aminooxy-2,4-dinitro-benzene or with alkylatingagents of the general formula (VIII)

X²−A¹  (VIII)

 in which

A¹ represents optionally substituted alkyl and

X² represents halogen or the grouping —O—SO₂—O—A¹,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

and electrophilic or nucleophilic and/or oxidation or reductionreactions within the scope of the definition of the substituents are, ifappropriate, subsequently carried out in a customary manner.

The compounds of the general formula (I) can be converted by customarymethods into other compounds of the general formula (I) according to theabove definition, for example by etherification or ether cleavage (X,Y:OH→OC₂H₅, OCH₃→OH), esterification or hydrolysis (for example X:OCH₂COOH→OCH₂COOC₂H₅, OCH(CH₃)COOCH₃→OCH(CH₃)COOH), reaction withdicyano or hydrogen sulphide (for example R⁵: Br→CN, CN→CSNH₂),conversion of carboxyl compounds into other carboxylic acid derivativesby customary methods (for example R²: COOH→CN, COOH→COOCH₃), conversionof sulfonic acid derivatives according to customary methods (for exampleX,Y: SO₃Na→SO₂Cl, SO₂Cl→SH), halogenation (for example X,Y: CH₃→CH₂Cl orCH₂Br)—cf. the Preparation Examples.

Using, for example,1-(4-cyano-2,5-difluoro-phenyl)-4-chlorodifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and 5-methoxy-1-naphthol as starting materials, thecourse of the reaction of process (a) according to the invention can beillustrated by the following formula scheme:

Using, for example, methyl 3-amino-4,4,4-trifluoro-crotonate and4-cyano-2-fluoro-5-(2-naphthyloxy)-phenyl isocyanate as startingmaterials, the course of the reaction in the process (b) according tothe invention can be illustrated by the following scheme:

Using, for example, methyl[1-(2,4-dichloro-5-(1-naphthylthio)-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamateas starting material, the course of the reaction in the process (c)according to the invention can be illustrated by the following formulascheme:

Using, for example,1-[2-chloro-4-trifluoromethyl-5-(6-methoxycarbonylmethoxy-2-naphthyloxy)-phenyl]-4-difluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineand methyl bromide as starting materials, the course of the reaction inthe process (d) according to the invention can be illustrated by thefollowing formula scheme:

The formula (II) provides a general definition of thehalogenophenyluracils to be used as starting materials in the process(a) according to the invention for preparing compounds of the formula(I). In the formula (II), R¹, R², R³, R⁴ and R⁵ each preferably havethose meanings which have already been mentioned above, in connectionwith the description of the compounds of the formula (I) according tothe invention, as being preferred, particularly preferred, veryparticularly preferred or most preferred for R¹, R², R³, R⁴ and R⁵; X¹preferably represents fluorine or chlorine, in particular fluorine.

The starting materials of the general formula (II) are known and/or canbe prepared by processes known per se (cf. EP-A-648749).

The formula (III) provides a general definition of the naphthalenederivatives further to be used as starting materials in the process (a)according to the invention. In the formula (III), m, n, Q, X and Y eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the formula (I)according to the invention, as being preferred, particularly preferred,very particularly preferred or most preferred for m, n, Q, X and Y.

The starting materials of the general formula (III) are known organicchemicals for synthesis.

The formula (IV) provides a general definition of the aminoalkenoic acidesters to be used as starting materials in the process (b) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (IV), R² and R³ each preferably have those meaningswhich have already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for R² and R³; R preferably representsC₁-C₄-alkyl, phenyl or benzyl, in particular methyl or ethyl.

The starting materials of the general fonnula (IV) are known and/or canbe prepared by processes known per se (cf. J. Heterocycl. Chem. 9(1972), 513-522).

Formula (V) provides a general definition of the aryl isocyanatesfurther to be used as starting materials in the process (b) according tothe invention. In the general formula (V), m, n, Q, R⁴, R⁵, X and Y eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred, very particularly preferred or most preferred for m, n, Q,R⁴, R⁵, X and Y.

The starting materials of the general formula (V) have hitherto not beendisclosed in the literature; as novel compounds, they also form part ofthe subject-matter of the present application.

The novel aryl isocyanates of the general formula (V) are obtained byreacting aniline derivatives of the general formula (IX)

in which

m, n, Q, R⁴, R⁵, X and Y are each as defined above

with phosgene in the presence of a diluent, such as, for example,chlorobenzene, at temperatures between −20° C. and +150° C. (cf., forexample, also EP-A-648749).

The formula (VI) provides a general definition of the arylurethanes tobe used, if appropriate, as starting materials in the process (b)according to the invention. In the general formula (VI), m, n, Q, R⁴,R⁵, X and Y each preferably have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferred,particularly preferred, very particularly preferred or most preferredfor m, n, Q, R⁴, R⁵, X and Y; R preferably represents C₁-C₄-alkyl,phenyl or benzyl, in particular methyl or ethyl.

The starting materials of the general formula (VI) have hitherto notbeen disclosed in the literature; as novel compounds, they also formpart of the subject-matter of the present application.

The novel arylurethanes of the general formula (VI) are obtained byreacting aniline derivatives of the general formula (IX)

in which

m, n, Q, R⁴, R⁵, X and Y are each as defined above,

with chlorocarbonyl compounds of the general formula (X)

RO—CO—Cl  (X)

in which

R is as defined above,

if appropriate in the presence of an acid acceptor, such as, forexample, pyridine, and if appropriate in the presence of a diluent, suchas, for example, methylene chloride, at temperatures between −20° C. and+100° C. (cf. the Preparation Examples).

The aniline derivatives of the general formula (IX) required asprecursors have hitherto not been disclosed in the literature; as novelcompounds, they also form part of the subject-matter of the presentapplication.

The novel aniline derivatives of the general formula (IX) are obtainedby reacting anilines of the general formula (XI)

in which

R⁴, R⁵ and X¹ are each as defined above,

with naphthalene derivatives of the general formula (III)

 in which

m, n, Q, X and Y are each as defined above,

or with alkali metal salts of compounds of the formula (III)

if appropriate in the presence of a reaction auxiliary, such as, forexample, sodium hydride, and if appropriate in the presence of adiluent, such as, for example, N-methyl-pyrrolidone, at temperaturesbetween 0° C. and 150° C. (cf. the Preparation Examples).

The formula (VII) provides a general definition of theN-aryl-1-alkoxycarbonylamino-maleimides to be used as starting materialsin the process (c) according to the invention for preparing compounds ofthe general formula (I). In the general formula (VII), m, n, Q, R³, R⁴,R⁵, X and Y each preferably have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferred,particularly preferred, very particulaly preferred or most preferredform, n, Q, R³, R⁴, R⁵, X and Y; R⁶ preferably represents C₁-C₄-alkyl,in particular methyl or ethyl.

The novel N-aryl-1-alkoxycarbonylamino-maleimides of the general formula(VII) are obtained by reacting alkyl(2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula(XII)

in which

R³ is as defined above and

R′ represents alkyl, (in particular methyl or ethyl),

with aniline derivatives of the general formula (IX)

 in which

m, n, Q, R⁴, R⁵, X and Y are each as defined above,

if appropriate in the presence of a diluent, such as, for example,acetic acid, at temperatures between 0° C. and 200° C., preferablybetween 50° C. and 150° C.

The precursors of the general formula (XII) are known and/or can beprepared by processes known per se (cf. DE 19604229).

The formula (Ia) provides a general definition of the substitutedphenyluracils to be used as starting materials in the process (d)according to the invention for preparing compounds of the formula (I).In the formula (Ia), m, n, Q, R², R³, R⁴, R⁵, X and Y each preferablyhave those meanings which have already been mentioned above, inconnection with the description of the compounds of the formula (I)according to the invention, as being preferred, particularly preferred,very particularly preferred or most preferred for m, n, Q, R², R³, R⁴,R⁵, X and Y.

As novel substances, the starting materials of the general formula (Ia)for process (b) also form part of the subject-matter of the presentapplication; they can be prepared according to processes (a), (b) and(c) according to the invention.

The formula (VIII) provides a general definition of the alkylatingagents further to be used as starting materials in the process (d)according to the invention. In the formula (VIII), A¹ preferablyrepresents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkylhaving 1 to 4 carbon atoms and X² represents chlorine, bromine, iodine,methylsulphonyloxy or ethylsulphonyloxy; A¹ particularly preferablyrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl and X²represents chlorine, bromine, iodine, methylsulphonyloxy orethylsulphonyloxy.

The starting materials of the formula (VIII) are known organic chemicalsfor synthesis.

The processes according to the invention for preparing the compounds ofthe general formula (I) are preferably carried out using diluents.Suitable diluerits for carrying out the processes (a), (b), (c) and (d)according to the invention are, in addition to water, especially inertorganic solvents. These include, in particular, aliphatic, alicyclic oraromatic, optionally halogenated hydrocarbons, such as, for example,benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene,petroleum ether, hexane, cyclohexane, dichloromethane, chloroform,carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethyleneglycol diethyl ether; ketones, such as acetone, butanone or methylisobutyl ketone; nitriles, such as acetonitrile, propionitrile orbutyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

Suitable reaction auxiliaries for the processes (a), (b), (c) and (d)according to the invention are, in general, the customary inorganic ororganic bases or acid acceptors. These preferably include alkali metalor alkaline earth metal acetates, amides, carbonates, bicarbonates,hydrides, hydroxides or alkoxides, such as, for example, sodium acetate,potassium acetate or calcium acetate, lithium amide, sodium amide,potassium amide or calcium amide, sodium carbonate, potassium carbonateor calcium carbonate, sodium bicarbonate, potassium bicarbonate orcalcium bicarbonate, lithium hydride, sodium hydride, potassium hydrideor calcium hydride, lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- ori-propoxide, n-, i-, s- or t-butoxide, or potassium methoxide, ethoxide,n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basicorganic nitrogen compounds, such as, for example, trimethylamine,triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexyl-amine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine,1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

Other suitable reaction auxiliaries for the processes according to theinvention are phase-transfer catalysts. Examples of such catalysts whichmay be mentioned are:

Tetrabutylammonium bromide, tetrabutylammonium chloride,tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate,methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride,hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride,benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide,benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride,benzyl-tributylammonium bromide, tetrabutyl-phosphonium bromide,tetrabutylphosphonium chloride, tributyl-hexadecyl-phosphonium bromide,butyl-triphenylphosphonium chloride, ethyl-trioctyl-phosphonium bromide,tetraphenylphosphonium bromide.

When carrying out the processes (a), (b), (c) and (d) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably if between 10° C. and 120° C.

The processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to carry out theprocesses according to the invention under elevated or reducedpressure - in general between 0.1 bar and 10 bar.

For carrying out the process according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible for one of the components to be used in arelatively large excess. The reaction is generally carried out in asuitable diluent in the presence of a reaction auxiliary, and thereaction mixture is generally stirred at the required temperature forseveral hours. Work-up is carried out by customary methods (cf. thePreparation Examples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.By weeds in the broadest sense there are to be understood all plantswhich grow in locations where they are undesired. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolwlus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

Depending on the concentration, the active compounds according to theinvention are suitable for total weed control, for example on industrialterrain and railway tracks and on paths and areas with or without treegrowth. Equally, the active compounds according to the invention can beemployed for controlling weeds in perennial crops, for example forests,ornamental tree plantings, orchards, vineyards, citrus groves, nutorchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantings and hop fields, on lawns and turf and pastures and forselective weed control in annual crops.

The active compounds of the formula (I) according to the invention havestrong herbicidal activity and a broad activity spectrum when used onthe soil and on above-ground parts of plants. To a certain extent, theyare also suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspo-emulsion concentrates,natural and synthetic substances impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is to say liquid solventsand/or solid carriers, optionally with the use of surfactants, that isto say emulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Liquid solvents which are mainlysuitable are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andwater.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates andprotein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use dyestuffs, such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyestuffs, suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients, such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate,flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl),flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl,-sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl),flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen,glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen,haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone,imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron,metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propisochlor,propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl),rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, sulfosulfuiron, tebutam, tebuthiuron,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin and triflusulfuron.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

4.04 g (25 mmol) of 1,5-dihydroxy-naphthalene are initially charged in100 ml of dimethyl sulphoxide and admixed with 2.5 g (25 mmol) of sodiumhydride (60%), and the mixture is stirred for 30 minutes. 8.0 g (25mmol) of1-(4-cyano-2,5-difluoro-phenyl)-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineare then added and the reaction mixture is stirred at from 60° C. to 70°C. for 20 hours and then poured into about the same amount of 2Nhydrochloric acid. The resulting crystalline product is isolated byfiltration with suction and purified by column chromatography (silicagel, chloroform/ethyl acetate, vol. 1:1).

This gives (as second fraction) 2.9 g (25% of theory) of4-(2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-1(2)pyrimidinyl)-5-fluoro-2-(5-hydroxy-1-naphthyloxy)-benzonitrileof melting point 168° C.

Example 2

A mixture of 32.6 g (71 mmol) of4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(5-hydroxy-1-naphthyloxy)-benzonitrile(cf. Example 1), 19.8 g (71 mmol) of dimethyl sulphate, 21.7 g (71 mmol)of potassium carbonate and 200 ml of acetone is stirred and heated underreflux for 20 hours. After cooling to room temperature, the mixture isconcentrated under water-pump vacuum, the residue is shaken with ethylacetate/1N hydrochloric acid and the organic phase is separated off,washed with water, dried with sodium sulphate and filtered. The filtrateis concentrated under water-pump vacuum, the residue is digested withdiethyl ether/petroleum ether and the resulting crystalline product isisolated by filtration with suction and purified by columnchromatography (silica gel, chloroform/ethyl acetate, vol. 3:1).

This gives (as first fraction)5-fluoro-2-(5-methoxy-1-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrileof melting point 109° C.

Example 3

3.63 g (25 mmol) of 2-naphthol are initially charged in 100 ml ofdimethyl sulphoxide and admixed with 2.5 g (25 mmol) of sodium hydride(60%), and the mixture is stirred for 30 minutes. 8.0 g (25 mmol) of1-(4-cyano-2,5-difluoro-phenyl)-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineare then added and the reaction mixture is stirred at from 60° C. to 70°C. for 20 hours and then poured into about the same amount of 2Nhydrochloric acid. The resulting crystalline product is isolated byfiltration with suction.

This gives 9.6 g (86% of theory) of4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(2-naphthyloxy)benzonitrileof melting point 92° C.

Example 4

A mixture of 2.7 g (5.91 mmol) of4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(6-hydroxy-2-naphthyloxy)benzonitrile,0.89 g (5.91 mmol) of dimethyl sulphate, 0.98 g (5.91 mmol) of potassiumcarbonate and 100 ml of acetone is stirred and heated under reflux for20 hours. After cooling to room temperature, the mixture is concentratedunder water-pump vacuum, the residue is shaken with ethyl acetate/1Nhydrochloric acid and the organic phase is separated off, washed withwater, dried with sodium sulphate and filtered. The residue is digestedwith diethyl ether/petroleum ether and the resulting crystalline productis isolated by filtration with suction and purified by columnchromatography (silica gel, chloroform/ethyl acetate,. vol. 2:1).

This gives (as second fraction) 0.8 g (29% of theory) of5-fluoro-2-(6-hydroxy-2-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrileof melting point 174° C.

Example 5

A mixture of 0.25 g (0.53 mmol) of5-fluoro-2-(7-hydroxy-2-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrile,0.11 g (0.53 mmol) of ethyl 2-bromo-propanoate (racemic), 0.10 g (0.53mmol) of potassium carbonate and 30 ml of acetonitrile is stirred andheated under reflux for 18 hours. Afler cooling to room temperature, themixture is concentrated under water-pump vacuum, the residue is shakenwith ethyl acetate/1N hydrochloric acid and the organic phase isseparated off, washed with saturated aqueous sodium chloride solution,dried with sodium sulphate and filtered. The filtrate is concentratedunder water-pump vacuum, the residue is digested with diethyl ether andthe resulting crystalline product is isolated by filtration withsuction.

This gives 0.15 g (50% of theory) of ethyl2-[7-(2-cyano4-fluoro-5-[3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl]-phenoxy)-2-naphthyloxy]-propanoate(racemate) of melting point 133° C.

Example 6

A mixture of 0.35 g (0.74 mmol) of5-fluoro-2-(6-hydroxy-2-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrile,0.22 g (0.74 mmol) of ethyl (R)-2-(p-tolyl-sulphonyloxy)-propanoate,0.13 g (0.74 mmol) of potassium carbonate and 30 ml of acetonitrile isstirred and heated under reflux for 20 hours. After cooling to roomtemperature, the mixture is concentrated under water-pump vacuum, theresidue is shaken with ethyl acetate/1N hydrochloric acid and theorganic phase is separated off, washed with saturated aqueous sodiumchloride solution, dried with sodium sulphate and filtered. The filtrateis concentrated under water-pump vacuum and the residue is purified bycolumn chromatography (silica gel, chloroform/ethyl acetate, vol. 2:1).

This gives 0.06 g (14% of theory) of ethyl(R)-2-[6-(2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl]-phenoxy)-2-naphthyl-oxy]-propanoateas an amorphous product (logP:3.99 at pH 2.3)

Analogously to Examples 1 to 6 and in accordance with the generaldescription of the preparation process according to the invention, it isalso possible to prepare, for example, the compounds of the generalformula (I) listed in the tables below.

Table 1: Examples of the compounds of the formula (I)

All examples in Table 1 refer to compounds in which Q represents O(oxygen) and R³ represents H (hydrogen).

Ex. No. Q R¹ R² R³ R⁴ R⁵

Physical Data 7 O CH₃ CF₃ H F CN

m.p.: 114° C. 8 O CH₃ CF₃ H F CN

m.p.: 126° C. (racemate) 9 O H CF₃ H F CN

m.p.: 76° C. 10 O CH₃ CF₃ H F CN

m.p.: 168° C. 11 O CH₃ CF₃ H F CN

m.p.: 205° C. 12 O H CF₃ H F CN

m.p.: 275° C. 13 O CH₃ CF₃ H F CN

m.p.: 161° C. 14 O CH₃ CF₃ H F CN

m.p.: 136° C. 15 O H CF₃ H F CN

(amorphous) 16 O CH₃ CF₃ H F CN

m.p.: 152° C. 17 O H CF₃ H F CN

m.p.: 158° C. 18 O CH₃ CF₃ H F CN

m.p.: 142° C. 19 O CH₃ CF₃ H F CN

m.p.: 130° C. 20 O CH₃ CF₃ H F CN

m.p.: 152° C. 21 O CH₃ CF₃ H F CN

22 O CH₃ CF₃ H F CN

23 O CH₃ CF₃ H F CN

m.p.: 164° C. 24 O CH₃ CF₃ H F CN

25 O CH₃ CF₃ H F CN

26 O CH₃ CF₃ H F CN

m.p.: 225° C. 27 O CH₃ CF₃ H F CN

m.p.: 151° C. (racemate) 28 O CH₃ CF₃ H F CN

29 O CH₃ CF₃ H F CN

(R enantiomer) 30 O CH₃ CF₃ H F CN

m.p.: 155° C. 31 O H

H F CN

logP = 2.11^(a)) 32 O H

H F CN

logP = 2.13^(a)) 33 O CH₃

H F CN

logP = 3.22^(a)) 34 O CH₃

H F CN

logP = 3.26^(a)) 35 O CH₃

H F CN

logP = 2.06^(a)) 36 O H CF₃ H F CN

m.p.: 156° C. 37 O H CF₃ H F CN

m.p.: 118° C. 38 O H CF₃ H F CN

m.p.: 96° C. 39 O CH₃ CF₃ H F CN

m.p.: 144° C. 40 O CH₃ CF₃ H F CN

m.p.: 131° C. 41 O CH₃ CF₃ H F CN

m.p.: 134° C. 42 O CH₃ CF₃ H F CN

m.p.: 164° C. 43 O CH₃ CF₃ H F CN

m.p.: 118° C. 44 O CH₃ CN H F CN

logP = 3.21^(a)) 45 O CH₃

H F CN

logP = 2.43^(a)) 46 O CH₃ CN H F CN

logP = 2.24^(a))

The logP values given in Table 1 were determined in accordance with EECDirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C 18). Temperature: 43°C.

(a) Mobile phases for the determination in the acidic range: 0.1%aqeuous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—the corresponding test results in Table1 are labelled^(a)).

(b) Mobile phases for the determination in the neutral range: 0.01 molaraqueous phosphate buffer solution, acetonitrile; linear gradient from10% acetonitrile to 90% acetonitrile—the corresponding test results inTable 1 are labelled^(b)).

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda-max values were determined using the UV spectra from 200 nmto 400 nm in the maxima of the chromatographic signals.

The compound listed above in Table 1 as Example 31 can be prepared, forexample, as follows:

13.0 g (27.4 mmol) of ethyl[1-(4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamateare dissolved in 200 ml of 1,4-dioxane, and a solution of 1.2 g (30mmol) of sodium hydroxide in 40 ml of water is added dropwise withstirring at room temperature (about 20° C.). The reaction mixture isthen stirred at 90° C. for 4 hours and subsequently concentrated underwater-pump vacuum. The residue is taken up in 800 ml of water andacidified using conc. hydrochloric acid. The resulting crystallineproduct is isolated by filtration with suction.

This gives 11.8 g (96% of theory) of1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylicacid.

The compound listed above in Table 1 as Example 33 can be prepared, forexample, as follows:

11.5 g (25.7 mmol) of1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine4-carboxylicacid are initially charged in 200 ml of acetone and admixed with 7.8 g(56 mmol) of potassium carbonate. At room temperature (about 20° C.), asolution of 8.1 g (64 mmol) of dimethyl sulphate in 20 ml of acetone isthen added dropwise with stirring, and the reaction mixture is heatedunder reflux for 4 hours. The mixture is subsequently concentrated underwater-pump vacuum, the residue is taken up in 600 ml of water andacidified with conc. hydrochloric acid and the resulting crystallineproduct is isolated by filtration with suction.

This gives 11 g (90% of theory) of methylI-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-3-methyl-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate.

The compound listed above in Table 1 as Example 35 can be prepared, forexample, as follows:

10.7 g (22.5 mmol) of methyl1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-3-methyl-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate are dissolved in 200 ml oftetrahydroflran and admixed successively with 10.3 g of ammoniumchloride and a 25% strength aqueous ammonia solution. The reactionmixture is stirred at room temperature (about 20° C.) for 12 hours andsubsequently concentrated under water-pump vacuum. The residue isstirred with hexane and the crystalline product is isolated byfiltration with suction.

This gives 9.4 g (91% of theory) of1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-3-methyl-1,2,3,6-tetrahydro-pyrimidine4-carboxamide.

PRECURSORS OF THE FORMULA (VI) Example (VI-1)

2.0 g (7.2 mmol) of 4-amino-5-fluoro-2-(2-naphthyloxy)-benzonitrile areinitially charged in 100 ml of acetone and, at 40° C., admixed dropwisewith stirring with 1.78 g (7.2 mmol) of trichloromethyl chloroformate(“diphosgene”). The reaction mixture is stirred at 40° C. for 4 hoursand then added dropwise with stirring to 100 ml of ethanol. The mixtureis then stirred at room temperature (about 20° C.) for 15 minutes andsubsequently concentrated under water-pump vacuum. The residue isstirred with diethyl ether/petroleum ether and the resulting crystallineproduct is isolated by filtration with suction.

This gives 0.4 g (16% of theory) of O-ethylN-[4-cyano-2-fluoro-5-(2-naphthyloxy)-phenyl]-carbamate of melting point132° C.

PRECURSORS OF THE FORMULA (VII): Example (VII-1)

A mixture of 15.0 g (48.7 mmol) of4-amino-5-fluoro-2-(6-methoxy-naphthalen-2-yl-oxy)-benzonitrile, 10.8 g(58 mmol) of ethyl (2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamate and 200ml of acetic acid is heated under reflux for 4 hours and subsequentlyconcentrated under water-pump vacuum. The residue is stirred with waterand the crystalline product is isolated by filtration with suction andpurified by column chromatography (silica gel, methylene chloride/ethylacetate, vol. 95/5).

This gives 13.5 g (58% of theory) of ethyl[1-(4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamate. logP=3.63)

Analogously to Example (VII-1), it is also possible to prepare, forexample, the compounds of the general formula (VII) listed in Table 2below.

TABLE 2 Examples of the compounds of the formula (VII) Ex. No. Q R² R³R⁴ R⁵

Physical Data VII-2 O C₂H₅ H F CN

logP = 3.67^(a)) VII-2 O C₂H₅ H F CN VII-3 O C₂H₅ H F CN VII-4 O C₂H₅ HF CN

PRECURSORS OF THE FORMULA (IX) Example (IX-1)

3.93 g (26 mmol) of 2-naphthol are initially charged in 150 ml ofN-methyl-pyrrolidone and mixed with 1.25 g (26 mmol) of sodium hydride(60%), and the mixture is stirred at room temperature (about 20° C.) for30 minutes and then admixed with 4.0 g (26 mmol) of4-amino-2,5-difluoro-benzonitrile and stirred at from 105° C. to 115° C.for two days. After cooling to room temperature, the mixture is pouredinto about the same amount of 2N hydrochloric acid, stirred for 15minutes and extracted with ethyl acetate. The organic phase is washedwith water, dried with sodium sulphate and filtered. The filtrate isconcentrated under water-pump vacuum, the residue is digested withdiethyl ether/petroleum ether and the crystalline product is isolated byfiltration with suction and purified by column chromatography (silicagel, chloroform/ethyl acetate, vol. 4:1).

This gives 1.0 g (14% of theory) of⁴-amino-5-fluoro-2-(2-naphthyloxy)-benzonitrile of melting point 89° C.

Analogously to Example (IX-1), it is also possible to prepare, forexample, the compounds of the general formula (IX) listed in Table 3below.

TABLE 3 Examples of the compounds of the formula (IX) Ex. No. Q R⁴ R⁵

Physical Data IX-2 O F CN

¹H-NMR (D₆-DMSO, δ): 8.03, 8.06 ppm IX-3 O F CN

m.p.: 130° C. IX-4 O F CN

m.p.: 144° C.

USE EXAMPLES Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of the spray liquor is chosen so that theparticular amount of active compound desired is applied in 1000 litresof water per hectare.

After three weeks the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, for example, the compounds of Preparation Examples 7, 8,10, 11 and 13 exhibit strong activity against weeds, and some of themare tolerated well by crop plants, such as, for example, maize.

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen so that the particular amounts of active compound desired areapplied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, for example, the compounds of preparation examples 7, 8,10, 11 and 13 exhibit strong activity against weeds.

What is claimed:
 1. A phenyluracil of the Formula (I)

m represents 0, 1 or 2, n represents 0, 1, 2 or 3, Q represents O(oxygen), S (sulphur), SO, SO₂, NH or N(C₁-C₄-alkyl), R¹ representshydrogen, amino or represents optionally cyano-, halogen- orC₁-C₃-alkoxy-substituted alkyl having 1 to 4 carbon atoms, R² representscarboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each caseoptionally cyano-, halogen- or C₁-C₃-alkoxy-substituted alkyl oralkoxycarbonyl having in each case 1 to 4 carbon atoms, R³ representshydrogen, halogen or represents optionally cyano-, halogen- orC₁-C₃-alkoxy-substituted alkyl having 1 to 4 carbon atoms, R⁴ representshydrogen, cyano, fluorine or chlorine, R⁵ represents cyano, carbamoyl,thiocarbamoyl, halogen or represents in each case optionallyhalogen-substituted alkyl or alkoxy having in each case 1 to 4 carbonatoms, X represents hydroxyl, mercapto, amino, nitro, formyl, cyano,carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl,halogenosulphonyl, represents optionally unsubstituted or cyano-,carboxyl-, carbamoyl-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-,C₁-C₄-alkoxy-carbonyl-, C₂-C₄-alkenyloxy-carbonyl-,C₂-C₄-alkinyloxy-carbonyl-, C₁-C₄-alkylamino-carbonyl-,di-(C₁-C₄-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-,phenylaminocarbonyl- or benzylaminocarbonyl- substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in eachcase 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl,alkoxycarbonyl, alkylaminocarbonyl, dial-kylaminocarbonyl,alkylcarbonyloxy, alkoxycarbonyloxy, alkylamino-carbonyloxy,dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxy-carbonylamino,alkylsulfonylamino, bis-alkylsulfonyl-amino orN-alkyl-carbonyl-N-alkylsulphonyl-amino having in each case 1 to 6carbon atoms in the alkyl groups, represents optionally unsubstituted orcyano-, carboxyl-, carbamoyl-, halogen-, C₁-C₄-alkoxy-carbonyl-,C₁-C₄-alkylamino-carbonyl- or di-(C₁-C₄-alkyi)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl,alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl oralkinylcarbonyloxy having in each case 2 to 6 carbon atoms in thealkenyl or alkinyl groups, or represents benzyloxy, and Y representshydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, representsoptionally unsubstituted or cyano-, carboxyl-, carbamoyl-, halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl-,C₁-C₄-alkylsulphonyl-, C₁-C₄-alkyl-carbonyl-, C₁-C4-alkoxy-carbonyl-,C₂-C₄-alkenyloxy-carbonyl-, C₂-C₄-alkinyloxy-carbonyl-, amino-carbonyl-,C₁-C₄-alkylaminocarbonyl-, di-(C₁-C₄-alkyl)-amino-carbonyl-,phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy,alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy,alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino,bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino havingin each case 1 to 6 carbon atoms in the alkyl groups, representsoptionally unsubstituted or cyanocarboxyl-, carbamoyl-, halogen-,C₁-C₄-alkoxycarbonyl-, C₁-C₄-alkylamino-carbonyl- or di-(C₁-C₄-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl,alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl oralkinylcarbonyloxy having in each case 2 to 6 carbon atoms in thealkenyl or alkinyl groups, or represents benzyloxy, where, in the casethat m and/or n are greater than 1, X and Y are identical or different,or salts of compounds of the Formula (I).
 2. A phenyluracil according toclaim 1 wherein m represents 0 or 1, n represents 0, 1 or 2, Qrepresents O (oxygen) or S (sulphur), R¹ represents hydrogen, amino orrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, R²represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, R³ represents hydrogen,fluorine, chlorine, bromine, or represents in each case optionallycyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, R⁴ represents hydrogen, fluorine or chlorine, R⁵represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,or represents in each case optionally fluorine- and/orchlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n-or i-propoxy, X represents hydroxyl, mercapto, amino, nitro, formyl,cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,sulphonyl, chlorosulphonyl, represents optionally unsubstituted orcyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s-or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-,propinyloxycarbonyl-, butinyloxycarbonyl-, methylaminocarbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-,benzyloxycarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methyl-sulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino,acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- oderi-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- ort-butoxy-carbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy,dimethyl-aminocarbonyloxy, diethylaminocarbonyloxy, acetylamino,propionylamino, n- or i-butyroylamino, methoxycarbonylamino,ethoxy-carbonylamino, n- or i-propoxycarbonylamino,methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino,or represents optionally unsubstituted or cyano-, carboxyl-, carbamoyl-,fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- ori-propylaminocarbonyl-, dimethylaminocarbonyl- ordiethylamino-carbonyl-substituted ethenyl, propenyl, butenyl,propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl,ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl,propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl,butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy orbutinecarbonyloxy, or represents benzoyloxy, Y represents hydroxyl,mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl,represents optionally unsubstituted or cyano-, carboxyl-, carbamoyl-,thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-,propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-,propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-,butinyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, diethylaminocarbonyl-, phenylaminocarbonyl- orbenzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propyl-sulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino,acetyl, propionyl, n- or i-butyroyl, methylcarbonyloxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl,ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy,methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy,methylaminocarbonyloxy, ethylamino-carbonyloxy, n- ori-propylaminocarbonyloxy, n-, i-, s- or t-butylamino-carbonyloxy,dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino,propionylamino, n- or i-butyroylamino, methoxycarbonyl-amino,ethoxycarbonylamino, n- or i-propoxycarbonylamino,methyl-sulphonylamino, ethylsulphonylamino, n- ori-propylsulphonylamino, or represents optionally unsubstituted orcyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl- or diethylamino-carbonyl-substituted ethenyl,propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl,butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy,butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy,propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy,propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy.
 3. Aphenyluracil according to claim 1 wherein m represents 0, n represents 0or 1, Q represents O (oxygen), R¹ represents hydrogen, amino or methyl,R² represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents ineach case optionally fluorine- and/or chlorine-substituted methyl,ethyl, methoxycarbonyl or ethoxycarbonyl, R³ represents hydrogen,fluorine, chlorine, bromine, or represents optionally fluorine- and/orchlorine-substituted methyl, R⁴ represents fluorine, R⁵ representscyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents in each case optionally fluorine- and/or chlorine-substitutedmethyl or methoxy, X represents hydroxyl, mercapto, amino, nitro,formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,bromine, sulphonyl, chlorosulphonyl, represents optionally unsubstitutedor cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- ori-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-, propenyloxycarbonyl-, methylaminocarbonyl-,ethylaminocarbonyl-, n- or i-propylamino-carbonyl-,dimethylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl,n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio,n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methyl-sulphonyl,ethylsulphonyl, methylamino, ethylamino, n- or i-propyl-amino,represents dimethylamino, diethylamino, acetyl, propionyl, n- ori-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, n- oder i-propylamino-carbonyl,dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n-or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamino-carbonyloxy, n-or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy,diethylaminocarbonyloxy, acetylamino, propionylamino, n- ori-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- ori-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- ori-propylsulphonylamino, or represents optionally unsubstituted orcyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethyl-aminocarbonyl- or diethylaminocarbonyl-substituted ethenyl,propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl,butenyloxy-carbonyl, ethinyl, propinyl, butinyl, propinyloxy,butinyloxy, propinyloxy-carbonyl or butinyloxycarbonyl, or representsbenzoyloxy, and Y represents hydroxyl, mercapto, amino, nitro, formyl,cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,sulpho, chlorosulphonyl, represents optionally unsubstituted or cyano-,carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-,methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- ori-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-,ethylsulfonyl-, acetyl-, propionyl-, n- or i-butyroyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,propenyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-,ethylaminocarbonyl-, n- or i-propylaminocarbonyl-,dimethylaminocarbonyl-, phenylaminocarbonyl- orbenzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methyl-sulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,methylamino, ethylamino, n- oder i-propylamino, representsdimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylaminocarbonyl, ethylamino-carbonyl, n- or i-propylaminocarbonyl,dimethylaminocarbonyl, diethyl-aminocarbonyl, acetyloxy, propinoyloxy,n- or i-butyroyloxy, methyl-carbonyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxy-carbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,dimethylaminocarbonyloxy, diethylamino-carbonyloxy, acetylamino,propionylamino, n- or i-butyroylamino, methoxycarbonylamino,ethoxycarbonylamino, n- or i-propoxycarbonyl-amino,methylsulphonylamino, ethylsulphonylamino, n- ori-propyl-sulphonylamino, or represents optionally unsubstituted orcyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,methylaminocarbonyl-, ethyl-aminocarbonyl-, n- ori-propylaminocarbonyl-, dimethylaminocarbonyl- or ordiethylaminocarbonyl-substituted ethenyl, propenyl, butenyl,propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl,ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonylor butinyloxycarbonyl, or represents benzoyloxy.
 4. A phenyluracilaccording to claim 1 wherein R² represents trifluoromethyl, R³represents hydrogen, and R⁵ represents cyano.
 5. A phenyluracilaccording to claim 1 wherein Q represents oxygen (O).
 6. A phenyluracilaccording to claim 1 wherein Y represents hydroxyl, methoxy, representsin each case methoxycarbonyl-, ethoxycarbonyl-, methylaminocarbonyl-,dimethyl-aminocarbonyl- and phenylaminocarbonyl-substituted methoxy andethoxy, represents methylaminocarbonyloxy, methylcarbonyloxy,propinyloxy, butinyloxy and ethoxycarbonyloxy.
 7. A compound of theFormula (Ia)

in which m, n, Q, R², R³, R⁴, R⁵, X and Y are each as defined inclaim
 1. 8. An herbicidal composition comprising an effective amount ofone or more compounds according to claim 1 and one or more extenders. 9.A method for controlling undesirable plants comprising the step ofallowing an effective amount of one or more compounds according to claim1 to act on a member selected from the group consisting of saidundesirable plants, a habitat of said undesirable plants andcombinations thereof.